DE69509379T2 - Substituierte phthalocyanine - Google Patents
Substituierte phthalocyanineInfo
- Publication number
- DE69509379T2 DE69509379T2 DE69509379T DE69509379T DE69509379T2 DE 69509379 T2 DE69509379 T2 DE 69509379T2 DE 69509379 T DE69509379 T DE 69509379T DE 69509379 T DE69509379 T DE 69509379T DE 69509379 T2 DE69509379 T2 DE 69509379T2
- Authority
- DE
- Germany
- Prior art keywords
- och2ch2
- trityl
- tert
- butyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000004973 liquid crystal related substance Substances 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 20
- -1 di-(tert-butyl)-phenoxy Chemical group 0.000 claims description 16
- 230000003287 optical effect Effects 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 150000002736 metal compounds Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000006096 absorbing agent Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 229910052745 lead Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 210000002421 cell wall Anatomy 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229910052758 niobium Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 150000003377 silicon compounds Chemical class 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 153
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- 239000002904 solvent Substances 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 239000000377 silicon dioxide Substances 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 239000003480 eluent Substances 0.000 description 23
- 230000007704 transition Effects 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 229920006391 phthalonitrile polymer Polymers 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KCDNQBCTPRALST-UHFFFAOYSA-N 4-dodecoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene-1,2-dicarbonitrile Chemical compound CCCCCCCCCCCCOC1=CC(C#N)=C(C#N)C=C1OCCOCCOCCOC KCDNQBCTPRALST-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 4
- XCJZOYQTGDDRLS-UHFFFAOYSA-N 1,2-dibromo-4-dodecoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene Chemical compound CCCCCCCCCCCCOC1=CC(Br)=C(Br)C=C1OCCOCCOCCOC XCJZOYQTGDDRLS-UHFFFAOYSA-N 0.000 description 3
- RISYVLILTAVNNP-UHFFFAOYSA-N 2-dodecoxyphenol Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1O RISYVLILTAVNNP-UHFFFAOYSA-N 0.000 description 3
- UIOMPGXXZDTCKJ-UHFFFAOYSA-N 4,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene-1,2-dicarbonitrile Chemical compound COCCOCCOCCOC1=CC(C#N)=C(C#N)C=C1OCCOCCOCCOC UIOMPGXXZDTCKJ-UHFFFAOYSA-N 0.000 description 3
- OKQCDTOHGKBHLR-UHFFFAOYSA-N 4,5-dihexadecylbenzene-1,2-dicarbonitrile Chemical compound CCCCCCCCCCCCCCCCC1=CC(C#N)=C(C#N)C=C1CCCCCCCCCCCCCCCC OKQCDTOHGKBHLR-UHFFFAOYSA-N 0.000 description 3
- NTZMSBAAHBICLE-UHFFFAOYSA-N 4-nitrobenzene-1,2-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C(C#N)=C1 NTZMSBAAHBICLE-UHFFFAOYSA-N 0.000 description 3
- 239000004976 Lyotropic liquid crystal Substances 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 238000002428 photodynamic therapy Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- QTTAHQYFRDNBSG-UHFFFAOYSA-N 1-dodecoxy-2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1OCCOCCOCCOC QTTAHQYFRDNBSG-UHFFFAOYSA-N 0.000 description 2
- GPFIBHBLYCONNS-UHFFFAOYSA-N 4,5-didodecoxybenzene-1,2-dicarbonitrile Chemical compound CCCCCCCCCCCCOC1=CC(C#N)=C(C#N)C=C1OCCCCCCCCCCCC GPFIBHBLYCONNS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- 101100350458 Oryza sativa subsp. japonica RR25 gene Proteins 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000002535 lyotropic effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 229920000867 polyelectrolyte Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- YDBAUWPGWGYZTF-UHFFFAOYSA-N 1,2-didecoxybenzene Chemical compound CCCCCCCCCCOC1=CC=CC=C1OCCCCCCCCCC YDBAUWPGWGYZTF-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SQDJAECYTSMKLT-UHFFFAOYSA-N 5-dodecoxy-6-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]isoindole-1,3-dione Chemical compound C1=C(OCCOCCOCCOC)C(OCCCCCCCCCCCC)=CC2=C1C(=O)NC2=O SQDJAECYTSMKLT-UHFFFAOYSA-N 0.000 description 1
- 241001177361 Breda Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229920003240 metallophthalocyanine polymer Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3488—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
- C09K19/3861—Poly(meth)acrylate derivatives containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0425—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect
- C09K2019/0429—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect the specific unit being a carbocyclic or heterocyclic discotic unit
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9405970A GB9405970D0 (en) | 1994-03-25 | 1994-03-25 | Substituted phthalocyanines |
| PCT/GB1995/000647 WO1995026381A1 (fr) | 1994-03-25 | 1995-03-23 | Phtalocyanines substitues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69509379D1 DE69509379D1 (de) | 1999-06-02 |
| DE69509379T2 true DE69509379T2 (de) | 1999-08-26 |
Family
ID=10752518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69509379T Expired - Fee Related DE69509379T2 (de) | 1994-03-25 | 1995-03-23 | Substituierte phthalocyanine |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5792860A (fr) |
| EP (1) | EP0751977B1 (fr) |
| JP (1) | JPH09511001A (fr) |
| KR (1) | KR100350816B1 (fr) |
| DE (1) | DE69509379T2 (fr) |
| GB (2) | GB9405970D0 (fr) |
| WO (1) | WO1995026381A1 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3836192B2 (ja) * | 1996-08-05 | 2006-10-18 | 株式会社リコー | フタロシアニン化合物 |
| JP2958454B2 (ja) * | 1998-03-12 | 1999-10-06 | 工業技術院長 | 液晶性フタロシアニンオキソチタニウム錯体 |
| ATE365170T1 (de) * | 2001-01-05 | 2007-07-15 | Seung-Yong Lee | Komplexverbindungen aus paramagnetischem metall und phthalocyanin und kontrastmittel, bei dem diese verbindungen verwendet werden |
| ES2244793T3 (es) * | 2001-03-21 | 2005-12-16 | L. MOLTENI & C. DEI FRATELLI ALITTI SOCIETA' DI ESERCIZIO SOCIETA' PER AZIONI | Analogos no centrosimetricos de ftalocianina sustituidos por metales, su preparacion y su utilizacion en terapia fotodinamica y diagnostico in vivo. |
| AU2003220791A1 (en) * | 2002-02-15 | 2003-09-16 | Mitsui Chemicals, Inc | Rewritable optical information recording medium and recording/reproducing method, recording/reproducing device |
| EP1534714B1 (fr) * | 2002-08-14 | 2007-05-16 | Ciba SC Holding AG | Afficheur a cristaux liquides et filtre couleur presentant une transparence amelioree a la lumiere verte |
| DE10253610A1 (de) * | 2002-11-15 | 2004-05-27 | Bayer Ag | Optische Datenspeicher enthaltend ein Co-Phthalocyanin mit einem axialen Substituenten und einem axialen Liganden in der mit Licht beschreibbaren Informationsschicht |
| US20070172624A1 (en) * | 2004-02-24 | 2007-07-26 | Heinz Wolleb | Optical recording materials writable using blue lasers |
| GB0420081D0 (en) * | 2004-09-10 | 2004-10-13 | Avecia Ltd | Phthalocyanines for ink-jet printing |
| US8178355B2 (en) * | 2008-09-15 | 2012-05-15 | Platypus Technologies, Llc. | Detection of vapor phase compounds by changes in physical properties of a liquid crystal |
| CN103275089B (zh) * | 2013-06-12 | 2015-08-05 | 长春理工大学 | 单羟乙氧基不对称氯代金属铟酞菁及其制备方法与应用 |
| JP6184902B2 (ja) * | 2014-05-30 | 2017-08-23 | 花王株式会社 | カーボンブラック分散液 |
| JP6362136B2 (ja) * | 2014-08-19 | 2018-07-25 | 国立研究開発法人物質・材料研究機構 | ポリスチレン含有アームを備えた金属フタロシアニン・コア型スターポリマー及びその製造方法 |
| EP3061775B1 (fr) | 2015-02-27 | 2018-12-12 | Canon Kabushiki Kaisha | Polymère comprenant une structure de phtalocyanine, procédé de fabrication du polymère, composition de pigment, dispersion de pigment et toner |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0749231B2 (ja) * | 1985-08-13 | 1995-05-31 | 三菱化学株式会社 | 光学記録体 |
| JPS62124987A (ja) * | 1985-11-27 | 1987-06-06 | Mitsubishi Chem Ind Ltd | 光学記録体 |
| GB8614673D0 (en) * | 1986-06-17 | 1986-07-23 | Secr Defence | Alkoxyphthalocyanines |
| EP0346354B1 (fr) * | 1987-02-13 | 1992-08-19 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Phthalocyanines substituees |
| JP2567022B2 (ja) * | 1988-03-15 | 1996-12-25 | 三井東圧化学株式会社 | 緑色フィルター |
| JPH0756019B2 (ja) * | 1988-12-15 | 1995-06-14 | 三井東圧化学株式会社 | 近赤外線吸収剤及びそれを用いた表示・記録材料 |
| DE59008355D1 (de) * | 1989-11-22 | 1995-03-09 | Ciba Geigy Ag | Substituierte Naphthalocyanine und deren Verwendung. |
| JP2946665B2 (ja) * | 1990-07-20 | 1999-09-06 | 三菱化学株式会社 | 光学記録媒体の製造方法 |
| DE69228502T2 (de) * | 1991-06-19 | 1999-08-12 | Mitsui Chemicals, Inc., Tokio/Tokyo | Phthalocyaninverbindungen und ihre Verwendung |
| JP3039030B2 (ja) * | 1991-09-04 | 2000-05-08 | 三菱化学株式会社 | フタロシアニン誘導体及び該誘導体を含有する光学記録体 |
| TW235298B (fr) * | 1992-02-27 | 1994-12-01 | Ciba Geigy | |
| US5348840A (en) * | 1993-05-05 | 1994-09-20 | Toyo Ink Manufacturing Co., Ltd. | Optical recording medium |
-
1994
- 1994-03-25 GB GB9405970A patent/GB9405970D0/en active Pending
-
1995
- 1995-03-23 US US08/700,405 patent/US5792860A/en not_active Expired - Fee Related
- 1995-03-23 GB GB9619102A patent/GB2302095B/en not_active Revoked
- 1995-03-23 DE DE69509379T patent/DE69509379T2/de not_active Expired - Fee Related
- 1995-03-23 KR KR1019960705462A patent/KR100350816B1/ko not_active IP Right Cessation
- 1995-03-23 WO PCT/GB1995/000647 patent/WO1995026381A1/fr active IP Right Grant
- 1995-03-23 JP JP7525030A patent/JPH09511001A/ja not_active Abandoned
- 1995-03-23 EP EP95912334A patent/EP0751977B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR970702328A (ko) | 1997-05-13 |
| GB2302095A (en) | 1997-01-08 |
| GB2302095B (en) | 1998-12-16 |
| US5792860A (en) | 1998-08-11 |
| GB9405970D0 (en) | 1994-05-11 |
| JPH09511001A (ja) | 1997-11-04 |
| EP0751977A1 (fr) | 1997-01-08 |
| KR100350816B1 (ko) | 2003-02-14 |
| EP0751977B1 (fr) | 1999-04-28 |
| GB9619102D0 (en) | 1996-10-23 |
| WO1995026381A1 (fr) | 1995-10-05 |
| DE69509379D1 (de) | 1999-06-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69509379T2 (de) | Substituierte phthalocyanine | |
| US6384027B1 (en) | Phthalocyanine analogs | |
| DE2937700C2 (de) | 2,3-Dicyano-hydrochinon-Derivate und Flüssigkristallmaterialien, die diese Derivate enthalten | |
| DE3686044T2 (de) | Optisches speichermedium. | |
| DE3927872C2 (de) | Dithiolat-Metallkomplexverbindungen, Verfahren zu ihrer Herstellung und sie enthaltendes optisches Informationsaufzeichnungsmaterial | |
| DE4234230C2 (de) | Substituierte Thieno[3,2-b]thiophene und ihre Verwendung | |
| EP0329613A2 (fr) | Matériaux organiques avec des propriétés optiques non linéaires | |
| DE3808430A1 (de) | Fluessigkristalline polymere mit chromophoren seitengruppen | |
| DE68916986T2 (de) | Dünnfilm aus organischem Farbstoff und Element aus organischem Dünnfilm. | |
| DE60010487T2 (de) | Chirale Dotierstoffe zur Erzeugung einer variablen Helixganghöhe und deren Anwendung in einer mehrfarbigen reflektierenden Anzeige | |
| DD200091A5 (de) | Fluessigkristallzusammensetzungen und ihre verwendung in anzeigevorrichtungen | |
| DE69727341T2 (de) | Phthalocyanine und ihre Verwendung als wiederbeschreibbares optische Aufzeichnungsmaterial | |
| DE69405984T2 (de) | Flüssigkristallpolymere | |
| DE60309041T2 (de) | Photochrome flüssig-kristalle | |
| DE69011341T2 (de) | Verfahren und gerät zur bilddatenverarbeitung. | |
| DE3688253T2 (de) | Herstellung und verwendung von purpurinen, chlorinen und purpurin und chlorin enthaltenden zubereitungen. | |
| US5942612A (en) | Substituted phthalocyanine liquid crystal compounds | |
| DE3883366T2 (de) | Flüssigkristall-Verbindung und Verfahren zu deren Herstellung, dieselbe enthaltende Flüssigkristallzusammensetzung und Flüssigkristall-Anzeigevorrichtung. | |
| DE69420169T2 (de) | Phthalocyaninverbindung und optisches Aufzeichnungsmedium das diese enthält | |
| DE60029293T2 (de) | Formazan-metallkomplexe | |
| DE3875877T2 (de) | Phthalocyaninverbindungen und ihre verwendung. | |
| DE69004811T2 (de) | Naphthalocyaninderivate, deren Herstellung, optisches Wiedergabe-Medium mit solchen Verbindungen und dessen Herstellung. | |
| DE3850283T2 (de) | Naphthalocyaninderivate und Verfahren zu ihrer Herstellung sowie optische Aufzeichnungsträger unter Verwendung dieser Derivate und Herstellungsverfahren hierfür. | |
| Houbrechts et al. | New organometallic materials for nonlinear optics: metal< sigma>-arylacetylides | |
| DE69929476T2 (de) | 5-ä(6-(2-fluorbenzyl)oxy-2-naphtyl)methylü-thiazolid in-2,4-dion kristallen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: QINETIQ LTD., LONDON, GB |
|
| 8339 | Ceased/non-payment of the annual fee |